Ethanol → HCID 9803983, compound

HRID 1646487Notes

Reaction equation

HRID 1646487 reaction equation
[CH2:1]([S:3]([CH2:6][CH2:7][C:8]([NH:10][NH:11][C:12]([N:14]1[CH2:20][C:19]2[CH:21]=[C:22]([O:25]C)[CH:23]=[CH:24][C:18]=2[O:17][C:16]2[CH:27]=[CH:28][C:29]([Cl:31])=[CH:30][C:15]1=2)=[O:13])=[O:9])(=[O:5])=[O:4])[CH3:2].B(Br)(Br)Br.C(O)C>C(Cl)Cl>[CH2:1]([S:3]([CH2:6][CH2:7][C:8]([NH:10][NH:11][C:12]([N:14]1[CH2:20][C:19]2[CH:21]=[C:22]([OH:25])[CH:23]=[CH:24][C:18]=2[O:17][C:16]2[CH:27]=[CH:28][C:29]([Cl:31])=[CH:30][C:15]1=2)=[O:13])=[O:9])(=[O:4])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 702EthanolHCID 25134Boron tribromideHCID 15229157HCID 15229157, compound

Product 1

HCID 9803983HCID 9803983, compoundYield 45.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred suspension of 8-chloro-2-methoxydibenz[b,f][1,4]oxazepine-10(11H)-carboxylic acid, 2-[3-(ethylsulfonyl)-1-oxopropyl]hydrazide (1.00 g), prepared in the manner described above in Example 3, in methylene chloride (5 mL) at approximately 5° C. (ice water bath) under nitrogen was added dropwise boron tribromide (1.0 M in 6.7 mL of methylene chloride). The ice bath was removed and the reaction stirred at room temperature for 3 hours. The reaction was carefully quenched by the addition of 1 N HCl, and poured into ethyl acetate (100 mL). The solution was washed once with 1 N HCl (100 mL). The 100 mL of 1 N HCl wash was extracted with ethyl acetate (100 mL). The ethyl acetate solutions were combined and washed with 1 N HCl, Water and brine. Evaporation of the solution in vacuo resulted in a semi-solid residue. This was treated With 10 mL of ethanol (3A) and heated on a steam bath for several minutes to break up the solid. Upon cooling, the solidified product Was collected by filtration. Recrystallization from ethanol (3A) yielded 0.44 g (45%) pure product as a white solid. Melting Point: 200°-202° C.

Workup

  1. customprepared in the manner
  2. customThe ice bath was removed
  3. customThe reaction was carefully quenched by the addition of 1 N HCl
  4. additionpoured into ethyl acetate (100 mL)
  5. washThe solution was washed once with 1 N HCl (100 mL)
  6. washThe 100 mL of 1 N HCl wash
  7. extractionwas extracted with ethyl acetate (100 mL)
  8. washwashed with 1 N HCl, Water and brine
  9. customEvaporation of the solution in vacuo
  10. customresulted in a semi-solid residue
  11. temperatureheated on a steam bath for several minutes
  12. temperatureUpon cooling
  13. filtrationthe solidified product Was collected by filtration
  14. customRecrystallization from ethanol (3A)

Sources & evidence

ORD record
ord-b57edebd9a0e4ca3a1bebbcab8288945
Source dataset
uspto-grants-1993_01
Patent number
US05180720

Reaction notes

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